methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

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Chemical Name:methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate
CAS No.:1344997-43-8
Molecular Formula:C₂₇H₃₀N₄O₂S
Molecular Weight:474.627
Hs Code.:

Synonyms:methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

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Chemical Property of methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

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Technology Process of methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

There total 13 articles about methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1344997-41-6
5-[5-(2-ethyl-3-formylphenyl)-1,3,4-thiadiazol-2-yl]-2-(2-methylpropyl)benzonitrile

: 343238-58-4
methyl azetidine-3-carboxylate

: 1344997-43-8
methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

Guidance literature:: 5-[5-(2-ethyl-3-formylphenyl)-1,3,4-thiadiazol-2-yl]-2-(2-methylpropyl)benzonitrile; methyl azetidine-3-carboxylate; With sodium acetate; acetic acid; In ethanol; at 20 ℃; for 0.166667h;

With sodium tris(acetoxy)borohydride; In dichloromethane;

Reference yield:

: 15126-06-4
methyl 3-iodo-4-hydroxybenzoate

: 1344997-43-8
methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 12 h / 140 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 25 °C

3.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water / 12 h / 100 °C / Inert atmosphere

4.1: water; lithium hydroxide / methanol / 4 h / 25 °C

4.2: pH 5

5.1: trichlorophosphate / 3 h / 90 °C

5.2: pH 8 - 9 / Cooling with ice

6.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 3 h / 20 °C

7.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 0.17 h / 120 °C / Microwave irradiation; Sealed vessel; Inert atmosphere

8.1: sodium acetate; acetic acid / ethanol / 0.17 h / 20 °C

With potassium phosphate; tert.-butylnitrite; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; copper(ll) bromide; lithium hydroxide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Suzuki Coupling / 7.1: Suzuki Coupling;

Reference yield:

: 108-36-1
1,3-dibromobenzene

: 1344997-43-8
methyl 1-[(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)methyl]-3-azetidinecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 4 h / -70 - -65 °C

2.1: n-butyllithium; isopropylmagnesium bromide / hexane; tetrahydrofuran / 1.17 h / 0 °C

2.2: 2 h / -10 - 20 °C

2.3: 0.17 h / 0 °C

3.1: hydrogenchloride / water; tetrahydrofuran / 1 h / 20 °C

4.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 80 °C

5.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 0.17 h / 120 °C / Microwave irradiation; Sealed vessel; Inert atmosphere

6.1: sodium acetate; acetic acid / ethanol / 0.17 h / 20 °C

With hydrogenchloride; potassium phosphate; n-butyllithium; isopropylmagnesium bromide; potassium acetate; sodium acetate; acetic acid; diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide; 5.1: Suzuki Coupling;